This skill should be used when the user asks to "plan a penetration test", "create a security assessment checklist", "prepare for penetration testing", "define pentest scope", "follow security testing best practices", or needs a structured methodology for penetration testing engagements.
Provide a comprehensive checklist for planning, executing, and following up on penetration tests. Ensure thorough preparation, proper scoping, and effective remediation of discovered vulnerabilities.
Reference Questions:
| Type | Purpose | Scope |
|---|---|---|
| External Pentest | Assess external attack surface | Public-facing systems |
| Internal Pentest | Assess insider threat risk | Internal network |
| Web Application | Find application vulnerabilities | Specific applications |
| Social Engineering | Test human security | Employees, processes |
| Red Team | Full adversary simulation | Entire organization |
| Factor | Consideration |
|---|---|
| Asset Value | Higher value = higher investment |
| Complexity | More systems = more time |
| Depth Required | Thorough testing costs more |
| Reputation Value | Brand-name firms cost more |
Budget Reality Check:
Environment Options:
Production - Realistic but risky
Staging - Safer but may differ from production
Clone - Ideal but resource-intensive
Common Pre-Scan Tools:
# Network vulnerability scan
nmap -sV --script vuln TARGET
# Web vulnerability scan
nikto -h http://TARGET
Cloud Provider Policies:
Evaluation Criteria:
| Factor | Questions to Ask |
|---|---|
| Experience | Years in field, similar projects |
| Methodology | OWASP, PTES, custom approach |
| Reporting | Sample reports, detail level |
| Communication | Availability, update frequency |
Testing Approaches:
| Type | Access Level | Simulates |
|---|---|---|
| Black Box | No information | External attacker |
| Gray Box | Partial access | Insider with limited access |
| White Box | Full access | Insider/detailed audit |
Report Should Include:
Monitoring Tools:
# Check security logs
tail -f /var/log/auth.log
tail -f /var/log/apache2/access.log
# Monitor network
tcpdump -i eth0 -w capture.pcap
Key Logs to Monitor:
Testing Frequency Factors:
□ Scope defined and documented
□ Authorization obtained
□ Environment prepared
□ Hosting provider notified
□ Team briefed
□ Monitoring enabled
□ Backups verified
□ Report received and reviewed
□ Findings prioritized
□ Remediation assigned
□ Fixes implemented
□ Verification testing scheduled
□ Environment cleaned up
□ Next test scheduled
**Target:** Corporate web application (app.company.com)
**Type:** Gray box web application pentest
**Duration:** 5 business days
**Excluded:** DoS testing, production database access
**Access:** Standard user account provided
# Enable comprehensive logging
sudo systemctl restart rsyslog
sudo systemctl restart auditd
# Start packet capture
tcpdump -i eth0 -w /tmp/pentest_capture.pcap &
| Issue | Solution |
|---|---|
| Scope creep | Document and require change approval |
| Testing impacts production | Schedule off-hours, use staging |
| Findings disputed | Provide detailed evidence, retest |
| Remediation delayed | Prioritize by risk, set deadlines |
| Budget exceeded | Define clear scope, fixed-price contracts |
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